21

Middletown, NY Homes for Sale under $400,000

Section Image Section Image
  • /25

    $360,000

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    71 Commonwealth Ave, Middletown, NY 10940

    Welcome to the perfect blend of comfort, character, and location. Nestled in the vibrant heart of Middletown, NY—just 70 miles from NYC—this beautifully updated home offers a peaceful retreat without sacrificing proximity. Whether you’re commuting for work or play, nearby transportation options, including the Metro-North train and major highways, make travel to the city a breeze. And when you're

    Agent Photo

    Brian Caplicki

    Keller Williams Hudson Valley

    (329) 212-0993

    71 Commonwealth Ave, Middletown, NY 10940
  • /22

    $350,000

    • 3 Beds
    • 1 Bath
    • 892 Sq Ft

    91 Mountain Ave, Middletown, NY 10940

    Looking for one-story living in a private dead end street, look no further as you have found it! Beautiful hardwood floors welcome you into a living room with plenty of window light followed by an eat-in kitchen that has been fully equipped with gorgeous stainless steel appliances, new counters and plenty of cabinet space. Three spacious bedrooms with plenty of closet space and a beautiful tiled

    Sandra Arnez Keller Williams Hudson Valley

    91 Mountain Ave, Middletown, NY 10940
  • /27

    $319,999

    • 3 Beds
    • 1.5 Baths
    • 1,248 Sq Ft

    6 Eaton Ct, Middletown, NY 10940

    Welcome to 6?Eaton Court, a bright and comfortable 3-bed, 1.5-bath townhouse nestled in a well-maintained Middletown community. With low-maintenance living made easy, this home is perfect for buyers who want to enjoy life — not worry about it. Step inside to find a smartly laid-out floor plan, where the living areas flow seamlessly and natural light fills the space. The three bedrooms offer

    Vincent Reda Keller Williams Realty

    6 Eaton Ct, Middletown, NY 10940
  • /30

    $359,999 Open Sat 1PM - 3PM

    • 3 Beds
    • 1.5 Baths
    • 1,160 Sq Ft

    5 Mills Ave, Middletown, NY 10940

    LOCATION, LOCATION, LOCATION! Don’t miss this charming 3 Bedroom, 1.5 Bathroom Two-Story Home located in the heart of Middletown and within the Middletown School District. This home offers unbeatable convenience—just minutes from local restaurants, shopping centers, banks, healthcare facilities, and postal services. Situated close to elementary and secondary schools, and just blocks from Orange

    Richard Baxter Keller Williams Realty

    5 Mills Ave, Middletown, NY 10940
  • /16

    $350,000

    • 3 Beds
    • 2.5 Baths
    • 930 Sq Ft

    65 Monhagen Ave, Middletown, NY 10940

    This beautifully updated Cape Cod–style single-family home offers 3 bedrooms and 2.5 baths, including a generous first-floor primary suite. The main level features a spacious living room with a fireplace, a formal dining room, and an elegant kitchen with granite and wood countertops along with stainless steel appliances. High ceilings, detailed moldings, a full bath, and a convenient laundry area

    Jonathon Lee Keller Williams Hudson Valley

    65 Monhagen Ave, Middletown, NY 10940
  • /33

    $350,000

    • 1 Bed
    • 1 Bath
    • 1,088 Sq Ft

    727 Route 17m, Middletown, NY 10940

    A Truly Unique Opportunity – Live, Work, or Both!Welcome to a property that perfectly blends charm, function, and versatility. This special offering is not only a wonderful place to call home but also provides incredible potential to operate your own business—all in a convenient, easily accessible location.Currently configured as a single-family residence with mixed-use potential, this

    Frank Muccari Cronin & Company Real Estate

    727 Route 17m, Middletown, NY 10940
  • /23

    $309,900

    • 2 Beds
    • 1 Bath
    • 836 Sq Ft

    36 Bert Crawford Rd, Middletown, NY 10940

    Price improved on this cute and cozy and very affordable, plus close to everything desirable home. This is a great starter home or perfect for downsizing. All original hardwood floors, large bathroom and a large rear deck leading to a quiet back yard to play and relax. Brand new hot water heater and newer roof and windows. This home is close to public transportation and stores and restaurants.

    Tom Pahucki Keller Williams Realty

    36 Bert Crawford Rd, Middletown, NY 10940
  • /36

    $314,900

    • 2 Beds
    • 2 Baths
    • 1,216 Sq Ft

    927 Tower Ridge Cir, Middletown, NY 10941

    Experience luxury, resort-style living at Tower Ridge Grande in the heart of Orange County. This beautifully positioned GROUND FLOOR Evergreen END-unit offers a most convenient location, a bright open layout, and refined finishes throughout, creating a home that feels both elegant and effortless. Walk right out of your unit directly to the dedicated parking space immediately in-front of the unit.

    Frank Muccari Cronin & Company Real Estate

    927 Tower Ridge Cir, Middletown, NY 10941
  • /43

    $329,000

    • 4 Beds
    • 2 Baths
    • 1,696 Sq Ft

    28 Spring St, Middletown, NY 10940

    Your Dream Home Awaits at 28 Spring St, Middletown.Don't let this second chance slip away. This beautiful, 4 bedroom, 2 bathroom home is back on the market. Previous buyer's financing fell through. This is an incredible opportunity for you to step right in and secure a truly remarkable property. The seller has invested in significant updates to make this home move-in ready. The inviting,

    Leidy Placido Howard Hanna Rand Realty

    28 Spring St, Middletown, NY 10940
  • /5

    $300,000

    • Land
    • 7 Acres
    • $42,857 per Acre

    2024 Mount Hope Rd, Middletown, NY

    Looking to build? Land available in prime location. Situated directly between Middletown and Town of Mount Hope with easy access to all major roadways. Zoned for residential and agriculture. Buyer/builder to subdivide 5-8 acres from this 37+ acre parcel as agreeable to seller and proposed in contract. Flat, open, cleared land may be suitable for 1-3 building lots. Land to purchase provides

    Amanda Ferrantello Hudson Valley Griffith

    2024 Mount Hope Rd, Middletown, NY
  • /33

    $375,000

    • 4 Beds
    • 2.5 Baths
    • 1,668 Sq Ft

    29 Little Ave, Middletown, NY 10940

    Discover this renovated colonial home nestled in the charming city of Middletown. This spacious single-family residence offers a perfect blend of classic charm and tasteful updates. The main level features a dedicated home office, an inviting living room, and an open-concept kitchen with stunning granite countertops and a center island. A formal dining room and a convenient half bath complete

    Michael LaMorte Christie's Int. Real Estate

    29 Little Ave, Middletown, NY 10940
  • /24

    $329,900

    • 3 Beds
    • 2 Baths
    • 1,056 Sq Ft

    9 Fairview Ave, Middletown, NY 10940

    A must see home! This beautiful colonial home will have everything brand new - from the exterior: roof, sidings, windows, porch, deck to the interior: kitchen, all walls with plumbing and electrical lines, kitchen with brand new cabinets, countertops and appliances: refrigerator, oven/range, microwave and dishwasher, beautiful bathrooms with tiles, hardwood floorings - all NEW. Featuring 3

    Anita S. Cristiano HomeSmart Homes & Estates

    9 Fairview Ave, Middletown, NY 10940
  • /2

    $350,000

    • 3 Beds
    • 1 Bath
    • 924 Sq Ft

    8 Hill Rd, Middletown, NY 10941

    Looking for a home you can make your own without breaking the bank? This 924 sq ft ranch style home on 4 private acres with direct Wallkill River access is a rare opportunity! This home needs some cleanup and finishing touches inside. You could move right in and update as you go! The Detached Garage needs a new roof and renovations. Perfect for FHA 203K buyers who want a little sweat equity and a

    Nancy LaBarbera Keller Williams Hudson Valley

    8 Hill Rd, Middletown, NY 10941
  • /14

    $341,999

    • 3 Beds
    • 1.5 Baths
    • 1,528 Sq Ft

    21 N Aspen Rd, Middletown, NY 10940

    Move-in ready 3-bedroom, 2-bath townhouse in the Middletown School District. Home features new roof and siding (2023), new windows, and great flooring throughout. No repairs needed! Gas heat (no oil), fenced-in backyard, and covered porch. Delivered vacant at closing. Convenient location near schools, parks, shopping, and major routes. Perfect turnkey property for homeowner or investor!

    Derek Greene Greene Realty Group

    21 N Aspen Rd, Middletown, NY 10940
  • /23

    $359,000

    • 2 Beds
    • 1.5 Baths
    • 1,115 Sq Ft

    14 Kensington Way, Middletown, NY 10940

    Welcome to this beautifully renovated townhouse-style condo offering 2 bedrooms and 1.5 bathrooms. The bright, open-concept kitchen features brand-new appliances and flows seamlessly into a spacious living room filled with natural light from the sliding glass doors. Step outside to a private backyard patio—perfect for relaxing or entertaining. Upstairs, you’ll find two well-designed bedrooms,

    Xiaohui Cui Keller Williams Hudson Valley

    14 Kensington Way, Middletown, NY 10940
  • /25

    $379,000

    • 2 Beds
    • 1 Bath
    • 1,142 Sq Ft

    390 Hufcut Rd, Middletown, NY 10941

    Light-filled home offering peace & serenity situated on a large, flat grassy lot. This warm home has many upgrades including new siding, almost new roof, many new windows, re-finished hardwood flooring, and more. Easy, one level living offers you a convenient layout with living room, dining room, two good size bedrooms, finished attic with extended living space(bedroom, office etc), unfinished

    Silvana Milinovich RE/MAX Prime Properties

    390 Hufcut Rd, Middletown, NY 10941
  • /41

    $399,000

    • 2 Beds
    • 1.5 Baths
    • 1,036 Sq Ft

    15 Clark St, Middletown, NY 10940

    Charming cape with water views on quiet street with boat launch! A total dream! House was recently renovated both inside and out. The recently painted rich, navy blue siding pops as you pull up alongside the newly built stone wall to welcome family and friends. The interior has been updated with new paint and flooring. Neutral colors and touches of shiplap throughout make the whole home very

    Hilary Ryan Goldman Howard Hanna Rand Realty

    15 Clark St, Middletown, NY 10940
  • /17

    $360,000

    • 4 Beds
    • 2 Baths
    • 1,796 Sq Ft

    24 Edinburgh Rd, Middletown, NY 10941

    Looking for something different? This spacious 4 bedroom 2 full bath contemporary raised ranch in the Town Of Wallkill just may be what you are looking for ! Open living room with cathedral ceilings & hardwood flooring. First floor primary bedroom & primary bath. Upper level has hardwood flooring through out with 3 bedrooms & a full bath. Family room on lower level. Rear deck overlooking your

    Ernie Acampora River Realty Services, Inc.

    24 Edinburgh Rd, Middletown, NY 10941
  • /8

    $330,000

    • 3 Beds
    • 2 Baths
    • 1,484 Sq Ft

    2 Rivervale Rd, Middletown, NY 10940

    Charming Corner Townhouse in Middletown – No HOA Fees!Welcome to 2 Riverdale Road, a delightful 3-bedroom, 1.5-bathroom townhouse nestled in the heart of Middletown, NY. This spacious 1,484 sq ft home offers a perfect blend of comfort and convenience, making it an ideal choice for families and first-time homebuyers.Key Features:Spacious Living: Enjoy the warmth of hardwood floors

    Kilimanjaro Toussaint YourHomeSold Guaranteed Realty

    2 Rivervale Rd, Middletown, NY 10940
  • /2

    $353,000

    • 3 Beds
    • 2 Baths
    • 1,545 Sq Ft

    187 Watkins Ave, Middletown, NY 10940

    Opportunity knocks at $353,000 in New York. Located near Sprucegate Farm, Swim King, and Magnanini Winery. This home has approx. 1,545 sq. ft. and a lot of approx. 7,750 sq. ft. A great investment opportunity. Buyers che

    Neven Spralja Real Home Services & Solutions, Inc

    187 Watkins Ave, Middletown, NY 10940
  • /44

    $319,999

    • 3 Beds
    • 2 Baths
    • 1,504 Sq Ft

    20 Benton Ave, Middletown, NY 10940

    Discover the potential in this charming 3-bedroom, 2-full-bath two-story home with 1,504 sq ft of living space. Full of character and solid construction, this property offers a formal dining room and plenty of room to grow with a full unfinished attic and full, unfinished, walk-out basement featuring washer/dryer hookups. Featuring strong bones and charming original touches, this home is brimming

    Vincent Reda Keller Williams Realty

    20 Benton Ave, Middletown, NY 10940

Home Trends in Middletown, NY

Housing Trends

Median Sale Price
$390,000
Median Single Family Sale Price
$415,000
Median Townhouse Sale Price
$409,500
Median 2 Bedroom Sale Price
$274,500
Median 1 Bedroom Sale Price
$177,500
Average Price Per Sq Ft
$245
Number of Homes for Sale
83
Last 12 months Home Sales
479
Months of Supply
2.10
Median List Price
$399,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
How to Buy a Home How to Finance a Home How to Sell a Home